While planning my rendezvous with Nick Jonas, I am hell-bent on getting him to do something totally, apocalyptically gay. Comeuppance, I think, for him jamming my social-media feeds with all those sexy photos. I suggest we take a flower-arranging class. His handlers kill that idea. Makeup lesson? Nope. Runway-walking course, in heels? Uh-uh. Nude male life drawing? Not a chance. Antiquing? Wings at Hooters? Getting shitfaced and eating steaks at a strip club? We settle on mini golf.

“What did you get up to last night?” I ask him after we meet and shake hands on New York’s West Side Highway, hoping to get the dish on some next-level hotel-room depravity — a dish that is, unfortunately, not on the menu.

“I was doing a listening session for my new music,” says Jonas, dressed in black skinny jeans and a black hoodie. Then he had a cigar—he loves cigars—and met friends at a dive bar.

Nick Jonas is quite laid-back. Vulnerable, even. In person, his charm—and that smoky, devastating gaze—actually comes off as shyness. Sometimes he seems a bit sorrowful, or shell-shocked.

We arrive at the mini-golf counter at Pier 25, in the TriBeCa neighborhood of Manhattan, where a nice, old, suspiciously overdressed Russian man asks what color balls we’d like.

“Hot pink!” I shout. “Nice,” Jonas says. He chooses orange, and when the Russian man asks if he can hold my balls as I fumble with my wallet, I make a sex joke. Jonas giggles. We’re off to a good start.

Jonas is an avid golfer back home in Los Angeles, where he shares a place with his brother Joe. The 23-year-old has a second home in Mammoth, Calif., a ski town where he enjoys snowboarding. He’s a bit of a jock. If he weren’t in entertainment, Jonas says, he would have pursued professional sports, probably baseball.

Like Persephone descending into the underworld, Jonas raises his hand and signals to his handlers—they call themselves Team Jonas—to remain outside the gates of the course. They obey, retiring behind black sunglasses to pound things into their phones. At the second hole, with another graceful flourish of his hand, he dismisses a pesky photographer who’s been buzzing around us.

Jonas was born in Texas and grew up in New Jersey. His father was a pastor with the Assembly of God church, his mother a sign language teacher. They met at Bible college in Dallas, where together they ran a sign language ministry called Signs of Love.

The actor-singer effectively launched his career at age 6, when he was in a salon with his mother and she prompted him to sing a ditty for the customers. A woman with her head in the shampoo bowl predicted that he could be a star and recommended an agent named Shirley. “It’s strange how clear that memory is,” Jonas says of that afternoon. “I was always singing. It was my favorite thing to do—still is, it turns out.”

He learned some show tunes, and within a couple of years was auditioning on Broadway. By age 10, Jonas had landed the role of Gavroche in Les Misérables. The idea of him playing a gruff, foulmouthed character on stage before thousands of spectators a night raised some eyebrows in his father’s congregation, which was staunchly conservative. (His parents have since left the church—his father initially resigned from the ministry to become Jonas’s manager. Jonas is no longer religious, but he maintains a strong relationship with God. “God is real to me,” he says.)

From Broadway he became a star on the Disney Channel, where he met his longtime close friend Demi Lovato, who, while working with him and his brothers on the Disney movie Camp Rock, dated his brother Joe. In 2005, Nick, Joe, and their older brother, Kevin, formed the Jonas Brothers. They toured with the Backstreet Boys, Miley Cyrus, and Avril Lavigne, and, before breaking up in 2013, recorded four studio albums and sold more than 17 million copies worldwide. Their last tour, in 2010, grossed $95 million.

“I loved music at an early age,” Jonas says. “[My parents] had no intention of pushing us to do it.” Still, he adds, “They were really open-minded and supportive.”

Jonas was pulled out of school in the third grade to focus on his career in entertainment and, while touring with the Jonas Brothers, had a teacher accompany him on the road. “It was a weird way to grow up, but I think I maintained some sense of normalcy,” he says.

Before he and his brothers formed the group, Jonas’s first single, “Dear God,” was played on Christian radio stations nationwide. The Jonas Brothers later gained popularity as a Christian band, though not an especially preachy one, playing bubblegum pop that appealed primarily to young girls. They wore “purity rings,” which they promoted to their fans, signs they’d taken a vow not to have sex before marriage. Their nonthreatening, squeaky-clean image appealed to parents, too—sometimes to a fault.

“The funny thing is, back in the day it used to be the parents who would be really aggressive,” Jonas says. Mothers and daughters were known to jump into the back of the brothers’ tour van. One time, a mom and daughter snuck into Jonas’s dressing room. He was a good sport: They ended up hanging out with the singer for more than an hour, pretending to be friends of a friend while Jonas played along.

As they grew older and looked to gain a broader audience, the brothers stripped their boy-next-door facade. In December 2013, two months after the band announced they were splitting up, Joe wrote in New York magazine that he’d had sex at age 20.

Less than a year later, the youngest Jonas all but nuked his chaste image. In September 2014, to promote his first post-group solo album, Nick Jonas, he made an appearance at the gay nightclub BPM in New York City and engaged in a partial striptease, unbuttoning his shirt for a crowd of adoring, half-naked, leather-clad patrons. Jonas also underwent an intense and rapid physical transformation for his role as a sexually conflicted wrestler on the Audience Network series Kingdom, consuming 4,200 calories a day to bulk up into the beefcake sex symbol of Instagram fame. He unveiled his new, jaw-dropping physique in a photo shoot for Flaunt magazine that October, his trousers around his knees while he grinned and grabbed his crotch in homage to Mark Wahlberg’s 1992 Calvin Klein campaign, one of the most famous underwear ads of all time.

As an album of R&B and pop, NickJonas received mostly positive reviews from critics, one of whom declared it as filling “the hole currently vacated by Justin Timberlake and Robin Thicke.” However, that same reviewer, echoing the sentiments of many, accused Jonas of taking “a page out of the James Franco playbook, courting the LGBT community, aggressively working both the gay press and New York City’s club circuit.”

The accusations of gay baiting and opportunism have left Jonas a bit wounded. “It’s not the majority, but a large handful have a negative opinion for whatever reason,” he says, “and I think it’s really quite sad.” Still, regardless of whether he’s playing footsie with the LGBT community, his work is starting to speak for itself.

Meanwhile, Nate, his character on Kingdom, is a man grappling with masculinity and a conservative family. In the finale of the first season, Nate has sex with a man in an alley behind a gay bar. Jonas’s performance on the show was surprising—absorbing and complex.

“It’s been a great character to play,” says Jonas, “one that I try to be respectful of and take myself out of. He’s on his own path.”

To prepare for the part, he spoke to some of his closest friends, some of whom were raised in conservative families, about their coming-out experiences. “It was a good way to research,” says Jonas, “to kind of build the character with some elements of real life.”

Playing Nate has been a springboard for his career, earning him newfound credibility. At one time, perhaps during those Disney days, this seemed unlikely. Agents told him he’d never be taken seriously as an actor because he was a Jonas.

But that’s changing. Jonas returns for the second part of Kingdom’s second season in June. He’ll also star in the upcoming James Franco–produced indie Goat, a coming-of-age film in which he plays a member of a fraternity whose hazing rituals become increasingly violent. The movie is a study of male aggression, carnal and testosterone-filled. Homoerotic, even.

A few weeks after our golf date, Jonas is back in New York and hosting a private listening party for his new album, Last Year Was Complicated, at the Dream Hotel, near Times Square. A couple dozen people are in attendance, the guests skewing heavily to young gay men of a certain boyish ilk.

Carmen Carrera, a transgender model and former RuPaul’s Drag Race contestant, glides into the room like a gazelle. Like Jonas, she has a magnetic, wounded-bird vibe about her. The two met the previous week at the GLAAD Media Awards, where Jonas presented Demi Lovato, his tour mate this summer, with the Vanguard Award, and Lovato made an odd joke about her dick being bigger than his. Jonas brings this moment up to the panting onlookers at the party, then throws them a bone, assuring them that, since Lovato dated his brother, she should know he’s doing just fine in that department.

Carrera doesn’t view Jonas’s flirting as insincere or self-serving. “I think he’s very humble and an amazing ally,” she says, leaning against the bar. “We need more people like him in the music industry—someone who’s willing to come out and say that he supports the entire LGBT community and embraces fans from all walks of life. And maybe he might have a trans love interest in one of his music videos. Let’s open up that conversation!” She pauses. “Also, we’re both from New Jersey, so we have a ton in common.”

Jonas continues to address the audience. “When I was working on this album, Jay Z asked me what it was about,” he announces. “I said it was about the past year of my life, and that the year was complicated. Jay Z said, ‘That’s the name of your album: Complicated.’ ”

The singer says that Last Year Was Complicated, out in June, is mostly about his split a year ago with former Miss USA Olivia Culpo (of Rhode Island). They were together two years.

“With this one I made a real point to tell stories as honestly as I could,” Jonas tells me. “It became very clear what it was going to be about, after the breakup. I just dove in headfirst and wrote about all of it. I think it was the most meaningful relationship I’ve ever been in, and it was the longest.”

He’s no stranger to having his romantic life dissected in the media. “It definitely sucks. It sort of feels like, on top of dealing with the situation with the person, you have to be thinking about other people’s opinion about it, and without all the information.”

When he was younger (and still a Jonas Brother), he found this attention rather creepy. “The fact that people were intrigued by a 14– or 15-year-old’s relationships was strange to me,” he says. “Now I think it makes a bit more sense. I think it’s kind of amusing, people’s interests. But it’s funny, because I think I live a pretty low-key life.”

One of the songs on the album, “Unhinged,” is about his inability to make decisions and commit. He had considered it for the title of the album before Jay Z intervened. But he thinks his wavering can also be a blessing: “It forces me to be as honest as I can in my lyrics.”

Because of his teen stardom, Jonas never went to college, something that seems to bother him. Had he gone, he would have liked to have studied English. “I’m not a huge reader,” he says sheepishly. “But I love to write. I guess writing lyrics is kind of like poetry.”

At the listening party, Jonas works the room, his baseball cap pulled down low over his eyes, his hands in his pockets, a swirl of middle-aged men in black whispering in his ear; twinks rows deep are pawing at him, demanding a selfie, trying to make an impression.

He seems sort of exhausted and lost, as if someone has always led him around by the shoulders and pushed him through doorways. As if now, with his rocketing solo career and him well on his way to becoming the next Justin Timberlake, something is coming to a head. It’s as if he’s in the middle of a realization, an acknowledgment, like he’s gaining true insight into his ridiculously bizarre and fortunate life and the role he’s had—or hasn’t had—in shaping it.